Changing Of Times And Chuck Bass
by Ariel0926
Summary: What if Chuck had asked Blair to leave that night? What if him and Jenny became friends that night.
1. Chapter 1

Chapter 1

A/n: This story was previously posted on my old acct. Angel67Demon. I am reposting and continuing. This story.

A/n: Part of this will be recognized from part of episode 3X22 Last Tango, Then Paris. So disclaimer on that. It's not mine it belongs to CW and its writers. Please review.

Chapter 1

"Are you ok?" Chuck asked feeling genuinely concerned.

Nothing. No response. Chuck sighed.

"You're welcome to stay the night." Chuck said regardless of the quiet.

"You're not kicking me out into the street?" Jenny decided to be a tad sarcastic, under the circumstances, "Lucky me."

She had wanted her first time to be special and in a way it was. Not that she would admit that out loud. At least not yet, and not to him.

Chuck sighed again. Perhaps this was going to be an even longer night then it had already been so far.

"Hey, most people don't get the offer." Chuck replied trying to show her that he wasn't as heartless as most people thought and that he did care for her.

Great, Jenny thought. Oh, well better than dragging my ass back home, to a family that hates me.

Chuck started to get back in bed. The elevator dinged.

Shit. They both thought together. Looking toward the living room.

"Nate?" Jenny whispered, looking at Chuck questioningly.

"Chuck?" Came Blair's distinctive voice.

Chuck went to get back out of bed.

"Chuck?" Came Blair's voice again. Getting closer and closer.

Chuck went to meet her by the door.

Jenny sat up.

"Blair?" Chuck asked, "What are you doing here?"

Jenny leaned over, Putting out the candle beside the bed. She really wasn't in the mood to deal with the consequences of Blair realizing she was there, alone with Chuck. Much less what they had just done.

Blair pulled the peonies out from behind her back, with a smirk on her face.

"You went." Chuck smirked back.

"Sorry I was so late."

"I waited."

"Dorota went into labor." Blair laughed, "She had her baby."

Chuck returned her laugh.

"I wasn't going to show up. I was resolved not to. Every bone in my body tried to slow me. Every voice in my head screamed don't."

"But?" Chuck asked getting very annoyed with her speech.

"But I didn't listen." Blair answered.

"Blair I think you should go." Chuck decided he didn't want to hear anymore. This wasn't how things should go. Especially not when committing your life to another person. They should want to be with you with every fiber of their being. You both should.

"But I showed up!"

"Please go." He walked her back to the elevator. Just wanting her to be gone, so he could think or not think.

"Bye, Chuck." She said, soundly slightly sad, as the door between them closed.

Chuck walked back to his room. Not seeing Jenny anywhere he called out.

"Jenny? Are you still here?" He hoped Blair hadn't caused her to leave.

No answer.

"Jenny?" He called again.

"I'm here." She called from his closet.

He opened the door. She was standing there holding her clothes, still wearing only her black slip.

"You know the closet is normally the first thing to be checked." He chuckled at her.

She rolled her eyes, half laughing, at his joke. Still, she knew it was an accurate statement.

"What happened with Blair?" She asked.

"I asked her to leave." He replied not really wanting to talk about it.

"Why?"

"I don't really want to talk about it."

"You sure? I can be a good listener if you need it."

"Not tonight. Maybe some other time. I don't even really want to think about it right now."

"Ok." She smiled, "But if you ever do… I'm always available."

Another pause of silence.

"So…" Was all Jenny could think to say, getting uncomfortable in the silence.

"Why don't we go back to my bed." Chuck replied seeing as they were still standing in his closet.

Jenny laughed, just now realizing where they still were. And allowed him to lead her back to his bed. His hand guiding her by the small of her back.

"So which would you prefer J, Talk, sleep, sex, or I'm always willing to hear your suggestions."

"Well… I'm really not tired. No to the sex, no offense I'm still sore, but talking is always nice."

"I'm sorry about that." And he did sound genuinely sorry.

"It's ok, it's be expected the first time."

"Speaking of that, I thought you lost it to Damien the drug dealer slash son of an ambassador, that I distinctly recall warning you against getting involved with."

"No, I just told everyone that and yea I recall your speech."

"Why if you don't mind my prying curiosity."

"I don't know really. I was already in so much trouble. And both Serena and Dan were making such a big deal out of it. So was everyone else really. So when I came home after telling Damien I wanted to wait and him abandoning me, So I lied to everyone."

"I'm sorry he did that."

"What's the worst thing Chuck Bass has ever done?" Jenny really just wanted to change the subject.

"I traded Blair for ownership of my hotel to my Uncle Jack."

"Wow." She laughed, "I honestly don't know what to say to that."

"It was horrible. I know and I knew it then. But I didn't actually think she would go through with it."

"Sometimes I miss how nice, innocent, naïve I used to be back before I started trying to change myself to try and prove my worth to Blair and everyone else in this world, really."

"I remember the first party I saw you at. You looked so cute in your dress. I really am sorry about trying to force myself on you. I was such a pompous ass back then, and nobody really ever seriously told me no. Not back then." He actually blushed at the compliment he gave her and looked truly ashamed from that incident.

"Bass I forgave you a long time ago, or else I wouldn't have stayed." A smile actually graced her lips. She had never seen him blush before.

"Thank you." He returned that smile, "I'm not sure I deserve it though."

They spent most of the night just talking.

For Chuck it was nice. He had never spent a night staying up with a girl just about nothing and everything all at once.

For Jenny it was nice as well, Nice to see another side of this man that was Chuck Bass, a side she was almost certain most people never saw or even knew existed.

Around 5am they both finally fell asleep, still just talking. Feeling completely satisfied with the night. It seemed like a perfect ending to what was a long and stressful day for them both.


	2. Chapter 2

Chapter 2

I own nothing. I was just struck with an idea of what if. Hope you like this chapter.

Chapter 2

Around 9 am the next morning Chuck was the first to awake.

Slowly recalling the previous night, he was surprised to say the least.

For one somehow during the night his arm had found its way around Jenny Humphrey and she was laying half across him half on her side, with her head up on his chest.

For two he had, had sex with her, both seemingly forgetting they were technically brother and sister. But only because Lily legally adopted him and then went and married Rufus. But it's not as bad as Serena and Dan sharing a half sibling.

Three, he had been planning to ask Blair to marry him yesterday, but by the time she had arrived here last night it didn't seem right anymore. So he decided to move on. And didn't want to think about it anymore.

And for now he was going to stop thinking at three.

He had a business meeting in two hours and he really needed to pee.

Slowly he worked his way out from under Jenny trying desperately not to wake her. In the process he couldn't help but notice how peaceful and angelic she looked in her slumber.

He really hope she wasn't still in pain from last night, and that she didn't regret it. He sure didn't. He may not have planned it but fate had a weird way of making things happen for a reason.

Not half an hour later, Jenny woke up. Feeling cold from the lack of heat from the body that had kept her warm throughout the night. Feeling disoriented from the lack of much sleep she walked out of Chuck's room looking for him.

"Chuck?"

"In the kitchen."

She followed his voice. Seeing him making pancakes. She smiled.

"Who knew, Chuck Bass, could cook his own food."

He laughed, "It's a secret, Not even Nate has seen me cook, but I was in the mood, and room service never puts cinnamon in their batter. Would you like some as well?"

"Oh, please." She smiled, "I'm starving and still quite tired. Hopefully the food will wake me up a bit."

"You're welcome to stay and sleep as long as you want, I have to leave in half an hour for a meeting."

"Thanks." She smiled, "but I should leave after I'm done. I wanna try and talk my out of sending me off to Hudson next year."

"Good luck, I hope you succeed. Would be nice to have you around next year."

He handed her a plate of food and sat and ate his own.

"Do you have any peanut butter?" Jenny asked smirking.

"Peanut butter?" Chuck was confused. But stood up to go get it anyway. "What do you need Peanut butter for?"

Another smirk, this one with a mischievous look to it.

"You'll see."

Intrigued, He handed it over along with a butter knife, watching her to see what she was going to do with it.

She spread it onto her pancakes, then poured tons of syrup on top.

He laughed, "I can honestly say never before have I seen anyone put peanut butter on their pancakes."

She laughed, "You see that's partially because girls of the Upper East Side are afraid of real food.", She winked, "But you should try it sometime."

"Seeing as I'm already almost done with these, perhaps I will next time. I have to admit I'm intrigued."

She smiled in between bites.

He finished and got up to go get dressed. He was running too late to have a shower, but the pancakes were totally worth it.

She finished as well and followed him into his room.

"Thanks for the pancakes, they were really good."

"No problem." Another smirk. "Just don't go telling everyone I can cook."

She laughed, "Who would believe me anyway."

"Touché, J"

She slipped her dress back on along with her shoes. She started to walk out of his room.

"Wait, Jenny, let me walk you out."

"You don't have to."

"No, I insist, It's the least I can do."

"Ok. Can't really see how it could hurt."

"Tell you what we can take my limo. I can just drop you off at the penthouse, it's on my way to my meeting anyway."

"Thanks, Chuck."

They walked down to his limo. He opened the door for her.

In no time at all she was home. Surprisingly he hugged her goodbye.

As she was getting out of the elevator to her home her phone buzzed.

Good luck persuading your dad. I had a nice time last night. –C

That actually made her smile inside. Then she braced herself. For the long heartfelt talk she was about to have with her dad and Lily.

Her Phone buzzed again.

Another Gossip Girl blast. Jenny rolled her eyes. It was a photo of her and Chuck just moments ago.

Spotted Little J receiving a hug from C. Was it brotherly or something more? I'll be watching and reporting back to you. Perhaps they spent the night together? Or perhaps this is all just a coincidence. And so soon after C rejected B. Maybe this is the reason?

A/n: Thanks so much for reading please review. :) Happy Holidays


	3. Chapter 3

Chapter 3

A/n: And special thanks for all of your reviews. Hope you like this chapter I was unsure about parts of it.

Chapter 3

When Jenny arrived to their home her dad and Lily were sitting on the couch talking.

They looked up hearing her come in.

"Where were you all night?" Rufus asked, fairly upset that she never came home last night.

"I went to Nate and Chuck's hoping to talk to Nate, But—"

"Nate wasn't there." Lily finished for her.

"No he wasn't, So I talked to Chuck—"

"What could you and Chuck possibly have to talk about, especially with your past!" This time it was Rufus' turn to interrupt.

Jenny sighed, loudly. Then took a deep breath.

"Dad, Lily, This is going to be a long talk. So, could you possibly, please stop interrupting me." She sounded sincere and pleading all in one.

Rufus and Lily looked at each other, both mirroring looks of curiosity. Lily was the one to answer.

"What is it that you want to say, Jenny?"

She paused recollecting herself and her courage.

She sat down across from them.

"Talking to Chuck last night, he helped me realize a lot of things, about myself, our family and really just everything that I've said and done since I've entered this world of privilege."

She paused to assess the reactions of her dad and the woman she was starting to think of as a motherly figure.

So far they both looked pleased and surprised all in one.

"Is Eric around? There are some things I want to say to him as well."

Lily answered, "No, actually he's out with Serena. They should be back in a few hours. Please continue though. Whatever you have to say to him you can say when he gets back."

"Not just to him, everyone really. But anyway, First of all I want to apologize for it all. I want to be a part of this family. I'm resolved to change to someone you could be proud to call your daughter."

"And just for you tough, for me as well. I—I no longer like the person I see when I look in the mirror and I haven't for some time now. I want to be someone I don't hate everything about."

Rufus had a sad look in his eyes. He had no idea his daughter had become so self-loathing.

"Now, I know you said I have to go to Hudson next year. And stay with my mom. I do hope you'll reconsider."

"Jenny, We are not going to allow you to manipulate us into changing our minds about you getting out of getting out of the Upper East Side."

She gave a sad sigh, "Dad I honestly hate that you would think that but at the same time I can't blame you with everything that I've done. But please before you send me off out right. Allow me to try and prove to you these aren't just more words. I don't need an answer right away. To try and prove I'm trying to change through my actions. Please just think about it and base it off the proof I know you will see the next few weeks left of school."

Just then Serena and Eric walked in.

"What's she doing here?" Serena asked, "I thought she had to stay in Brooklyn til' she was leaving."

Eric purposefully ignored her presence altogether.

Lily and Rufus stayed quiet hoping with everything that Jenny would stay true to her words and start by apologizing to Serena and Eric.

And she did, "Good, I'm glad you guys are here, I need to talk to you as well."

"I have nothing to say to you." You could just hear the scornful dislike in Serena's voice.

Eric still remained quiet.

Jenny looked at Serena pleadingly, "Please Serena, I know you hate me right now and you have every right, but please will you both just hear me out."

She looked pointedly at them both hoping Eric would at least acknowledge her.

"I'll hear you out." Eric replied shocking them all, "You're still my sister after all, but no promises."

"I couldn't begin to expect anything, I know I've been a bitch, especially to you Eric. Your my best friend and I've treated you horribly this last year. And I'm more sorry than you could ever know. I want to change."

Eric looked at her thoughtfully for a moment.

"You're on probation." He went and sat by his mother on the couch.

Jenny jumped up and hugged Eric, Lily, and Rufus. "Thank you so much, this means more to me then you could possibly know."

They all smiled on the inside, Except for Serena she was just annoying, Hoping that Jenny was indeed sincere in her moving forward to change.

"Well I hope you don't think I'm going to give in as easily with your show." Serena just had to try and be a killjoy.

Jenny looked up at her with a sad look, "I truly am sorry for everything I've don't and sad that has hurt you Serena. And if it would make you better I'll just go to Brooklyn for the remain—"

"No you won't, you'll stay here and live with Eric, Lily, and I. So we can keep an eye on you and see if you really mean it this time." Rufus was very forceful, so much so that no one even thought to argue against him.

There was a brief silence. Then Lily spoke up.

"You will continue to go to Constance, Eric will keep an eye on you there to make sure you mean what you say. And in a few weeks when school ends for the year. Rufus, you, and I will revisit you going to Hudson next year or not."

"Thank you so much Lily."

Serena glared, "I think I'll be going, forgive me if I don't jump for joy of your continued presence."

With that she was gone. It hurt Jenny that she wouldn't even give her a chance. But she didn't show it. And she couldn't exactly blame her after everything.

Jenny looked pointedly at her parents, "I really am sorry for all that I have done, I just want to be a better person. Someone you could be proud of and love."

Rufus grabbed Jenny in a strong, warm hug.

"Honey, I could never stop loving you. You're my little girl, always."

Jenny's eyes stung with slight tears at his words.

"I love you too, daddy."

"Hey, J, can I speak with you, alone, in my room?" Eric asked, he was still a little suspicious.

She nodded, and followed him to his room.

Before she could even start to say sorry to him again. He blurted out.

"Serena and I saw the gossip girl blast, is it true?"

"Yea, I went there looking for Nate, but he wasn't there."

"Yea, I know he was at the hospital with most everyone else."

"Oh, I didn't know that."

"Yea, Dorota had the baby."

"That I knew. Blair said as much to Chuck, before he asked her to leave."

"Were you the reason he asked her to leave?"

"I don't honestly know, we I don't think so. He said he didn't want to talk about it after she left."

"Did anything happen with you two? Did Blair even know you were there?"

Jenny blushed, "No she didn't know, but she probably does now thanks to Gossip Girl."

"But something happened?" It didn't go unnoticed that she avoided his first question.

She sighed, "Yea, umm, I, uhh, we were drinking and then… then I had sex with him for the first time. I know it was wrong but he thought Blair didn't love him anymore, and well I felt like everyone including my own father hated me."

Eric looked her confused, "Jenny were your family we may not like what you do sometimes but we still love you, besides I thought you and Damien?"

"No, I told him I wanted to wait, for my first time to be special, He told me I needed to grow up and stop acting like a little girl. Then he left. Thanks for you know, loving me even when I'm the worst sister ever." She had tears in her eyes threatening to spill over.

Eric hugged her, "Why did you lie? About Damien I mean."

"I don't know, I just wanted people to think I'm grown up I guess. Look, Eric, I want you to help. To help me at school. I'm relinquishing my thrown. Focusing on Parsons. And please don't tell anyone about Chuck. In a way it was a good thing. I think him and I are starting to become friends."

Eric was slightly surprised she was serious about changing. And even more surprised her and Chuck might be becoming friends. After everything. He hoped that friendship didn't come back to bite her in the ass.

"I need one of my two favorite brothers to help keep me in line." She smiled up at him, underneath tears.

"For you anything, Jenny." And he meant it.

"I mean it I don't ever wanna fall back into my old ways. Into everything I hate about myself."

Eric hugged her. Determined to do as she asked and help her.

A/n Please review with compliments, criticism, advice. Anything really. Much love to everyone that's taken the time to read my story so far. 3. I don't have the next chapter written yet. But I will try to have it up as soon as I do. Happy Holidays!


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